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2-(Trifluoromethyl)-4H-pyran-4-ones: Convenient, available and versatile building-blocks for regioselective syntheses of trifluoromethylated organic compounds

Abstract:

This review describes synthetic methods for the preparation of such modern and versatile building-blocks as 2-CF3-4-pyrones (2-(trifluoromethyl)-4H-pyran-4-ones), and their use in regioselective syntheses of various CF3-containing compounds. Synthesis of 2-CF3-4-pyrones bearing a substituent (substituents) at position(s) 3, 5 and 6, as well as regioselective preparation of trifluoromethylated 4(1H)-pyridin-4-one, benzo[c][1,6]naphthyridine, 4-thiopyrone, 2-quinaxolinone, diazepine, benzo[b][1,4]oxazin-2-one, pyrazole, 3-(pyrazolyl)indlole, pyrazolo[1,5-c]pyrimidine derivatives on the basis of these building-blocks has been described. The closest analogs of 2-CF3-4-pyrones, 2-RF-4-pyrones (RF = CF2H, C2F4H, C3F7, C4F9, C6F13, CF2CFCl2, CF2CHFCF3) has also been presented in the review. Due to unique regioselectivity, a strong regio-sensitivity to solvents and availability, 2-CF3-4-pyrones can be attributed to excellent starting or intermediate substrates for the preparation of various trifluoromethylated compounds. In contrast to other 2-RF-4-pyrones, 2-CF3-4-pyrones are more synthetically available and interact with nucleophiles usually more selectively.